Syringaldehyde

Base Information

• Chemical Name: Syringaldehyde
• CAS No.: 134-96-3
• Molecular Formula: C9H10O4
• Molecular Weight: 182.176
• Hs Code.: 29124900
• European Community (EC) Number: 205-167-5
• NSC Number: 41153
• UNII: 2ZR01KTT21
• DSSTox Substance ID: DTXSID2059643
• Nikkaji Number: J5.601D
• Wikipedia: Syringaldehyde
• Wikidata: Q411695
• Metabolomics Workbench ID: 67570
• ChEMBL ID: CHEMBL225303
• Mol file: 134-96-3.mol

Synonyms:2,6-dimethoxy-4-formylphenol;3,5-Dimethoxy-4-hydroxybenzaldehyde;SYAL;syringaldehyde

Chemical Property of Syringaldehyde

Chemical Property:

• Appearance/Colour: light yellow-green to brown crystalline powder
• Vapor Pressure: 0.000151mmHg at 25°C
• Melting Point: 110-113 °C(lit.)
• Refractive Index: 1.567
• Boiling Point: 322.1 °C at 760 mmHg
• PKA: 7.80±0.23(Predicted)
• Flash Point: 130.1 °C
• PSA: 55.76000
• Density: 1.234 g/cm³
• LogP: 1.22190
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: Chloroform, Methanol (Slightly)
• Water Solubility.: very sparingly soluble
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 182.05790880
• Heavy Atom Count: 13
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

Syringaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C=O
• Uses: Syringaldehyde is used in biological studies for the isolation and structural characterization of milled wood lignin, dioxane lignin, and cellulolytic lignin preparation from Brewer''s spent grain. Syringaldehyde may be used as an analytical reference standard for the determination of the analyte in guacoextracts and pharmaceutical preparations,(1) cognacs and wines,(2) plum brandies,(4) and wheat straw(5) by various chromatography techniques.

Technology Process of Syringaldehyde

There total 100 articles about Syringaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

syringic alcohol (530-56-3) → 2,6-dimethoxy-p-quinone (530-55-2,26547-64-8) + syringic aldehyde (134-96-3)

Guidance literature:

With oxygen; (pyridine)cobalt; In methanol; under 2585.7 Torr; Ambient temperature;

DOI:10.1021/jo00113a020

Reference yield: 61.0%

1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(4-methoxyphenoxy)-1,3-propanediol → 4-Methoxyphenylacetaldehyde (5703-26-4) + 4-methoxy-benzaldehyde (123-11-5) + syringic aldehyde (134-96-3)

Guidance literature:

With oxygen; vanadium(V) oxytriisopropoxide; In acetonitrile; at 25 - 40 ℃; for 12h; under 760.051 Torr; Irradiation; Sealed tube;

DOI:10.1021/acscatal.9b03768

Reference yield: 26.0%

trans-3,5-dimethoxy-4-hydroxycinnamic acid (530-59-6,7362-37-0) → syringic alcohol (530-56-3) + 3,5-dimethoxy-4-hydroxybenzoic acid (530-57-4) + syringic aldehyde (134-96-3)

Guidance literature:

With Stichococcus bacillaris 155LTAP; Microbiological reaction;

DOI:10.1016/S0040-4039(03)00458-1

upstream raw materials:

1,3-dimethoxy-2-hydroxy-benzene

4-acetoxy-3,5-dimethoxybenzaldehyde

hexamethylenetetramine

5-iodovaniline

Downstream raw materials:

5-(4-hydroxy-3,5-dimethoxy-benzylidene)-imidazolidine-2,4-dione

2-(4-hydroxy-3,5-dimethoxy-trans-styryl)-quinolin-8-ol

sinapinic acid

3-(4-acetoxy-3,5-dimethoxyphenyl)prop-2-enoic acid

Refernces

• 1、 Rao, Durvasula V.,Stuber, F. A.. "An Efficient Synthesis of 3,4,5-Trimethoxybenzaldehyde from Vanillin". . p. 308. Retrieved 1983.
• 2、 Pearl. "-". . p. 1746. Retrieved 1948.
• 3、 Cai,Arntfield,Charlton. "Structural changes of sinapic acid and sinapine bisulfate during autoclaving with respect to the development of colored substances". . p. 433 - 441. Retrieved 1999.
• 4、 DellaGreca, Marina,Pinto, Gabriele,Pollio, Antonino,Previtera, Lucio,Temussi, Fabio. "Biotransformation of sinapic acid by the green algae Stichococcus bacillaris 155LTAP and Ankistrodesmus braunii C202.7a". . p. 2779 - 2780. Retrieved 2003.
• 5、 Hawkins,Wright,Hibbert. "". . p. 2447. Retrieved 1937.
• 6、 Creighton,Hibbert. "". . p. 37. Retrieved 1944.
• 7、 Sharp. "-". . p. 852. Retrieved 1937.
• 8、 Creighton,Gibbs,Hibbert. "". . p. 32,35. Retrieved 1944.
• 9、 Zabiński, Jerzy,Wolska, Irena,Maciejewska, Dorota. "Comparison of structure in solid state of new 1,5-bis(4-cyano-2,6-dimethoxyphenoxy)alkanes by means of 13C CP/MAS NMR and X-ray diffraction". . p. 74 - 81. Retrieved 2007.
• 10、 Kumar, Kamlesh,Joshi, Penny,Rawat, Diwan S. "(±)-Camphor sulfonic acid assisted IBX based oxidation of 1° and 2° alcohols". . . Retrieved 2021/09/02.